Guidebook for Shelter Island
Sightseeing
Montauk
Public ocean beach, lighthouse, great town to visit
Havens House
16 S Ferry RdShelter Island history, hosts fairs and events.
Historic area of Shelter Island. See the old homes up on the hill ... Victoriana at its best. Local shops, restaurants.
9 locals recommend
Shelter Island Heights
Historic area of Shelter Island. See the old homes up on the hill ... Victoriana at its best. Local shops, restaurants.
A lovely vibrant walking village with many shops, restaurants, live theater, harbor, art galleries, etc. ... and just a short ferry ride away.
196 locals recommend
Sag Harbor
A lovely vibrant walking village with many shops, restaurants, live theater, harbor, art galleries, etc. ... and just a short ferry ride away.
Wonderful waterfront village, restaurants, great little shops, Greenport Brewing Co, Claudio's waterfront clam bar, just a ferry ride away by foot.
119 locals recommend
Greenport
Wonderful waterfront village, restaurants, great little shops, Greenport Brewing Co, Claudio's waterfront clam bar, just a ferry ride away by foot.
One of the most beautiful and famous vacation spots in the world, pristine villages, fantastic restaurants, white sand ocean beaches ... and celebs!
31 locals recommend
The Hamptons
One of the most beautiful and famous vacation spots in the world, pristine villages, fantastic restaurants, white sand ocean beaches ... and celebs!
Everything Else
Hiking for nature lovers. Trails and beautiful vistas cover one third of the island. Very safe, pristine. Take a trail map, and be back before the gates close!
70 locals recommend
Mashomack Preserve
79 S Ferry RdHiking for nature lovers. Trails and beautiful vistas cover one third of the island. Very safe, pristine. Take a trail map, and be back before the gates close!
Food Scene
Shelter Island House
11 Stearns Point RdGreat local resto and tavern.
The Pridwin
81 Shore RdGood food, fantastic views of the bay.
The hot-spot of Shelter Island for dining, star gazing, cocktails at the beach, etc. About a 10 minute walk. Might need a flashlight if walking at night.
93 locals recommend
Sunset Beach
Shore RdThe hot-spot of Shelter Island for dining, star gazing, cocktails at the beach, etc. About a 10 minute walk. Might need a flashlight if walking at night.
Lovely Italian/local restaurant in the heart of the historic Heights District.
6 locals recommend
Sweet Tomato's
15 Grand AvenueLovely Italian/local restaurant in the heart of the historic Heights District.
Vine Street Café
41 S Ferry RdHighly recommended restaurant in the center of the island.
Arts & Culture
On Shelter Island. Rehearsals and concerts by students and faculty directed by Itzhak Perlman, world famous violinist, offered free to the public. Not to be missed if you love music.
10 locals recommend
The Perlman Music Program
73 Shore RdOn Shelter Island. Rehearsals and concerts by students and faculty directed by Itzhak Perlman, world famous violinist, offered free to the public. Not to be missed if you love music.